Shelter Island Vacations

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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Mashomack Preserve.

Find hotels in Menantic Creek

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩932,631 per night from May 31 to Jun 1
₩932,631
₩1,278,634 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (780 reviews)
Stellar staff who made us feel most welcome. Loved the diversity of the team. Unforgettable scenery and experiences. We will definitely come back!

Reviewed on May 11, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩241,738 per night from May 19 to May 20
₩241,738
₩305,410 total
May 19 - May 20
includes taxes & fees
9.2/10 Wonderful! (1,344 reviews)
Cute place great views would go back in the summer

Reviewed on May 11, 2026

Montauk Manor
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is ₩114,945 per night from May 21 to May 22
₩114,945
₩132,195 total
May 21 - May 22
includes taxes & fees
8/10 Very Good! (1,004 reviews)
If you can look beyond the immediate exterior and sense of disrepair (it's not...), then you can enjoy the stay here. While there is no swimming pool, the property is well positioned to the coast and local beaches. They were doing some road construction immediately outside the property and on the ...

Reviewed on May 15, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,782 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.